Herman: What To Get Your Entrepreneur For the Holidays

SAI contributor Darren Herman is an entrepreneur and startup adviser based in New York (full bio after post). Darren writes the eponymous Darren Herman. He is tired of all you brilliant entrepreneurs looking like crap.

Entrepreneurs are a rare breed; we never seem to have enough time to finish our business plan, work on due diligence requests from VC’s, or stress test our upcoming release. But for whatever reason, we seem to have plenty of stuff.

This means:

t-shirts from 10 years ago,

pens from the 1 cent bin at CVS,

a single pair of shoes that have been to a combined 50 events (weddings, bar mitzvahs, trade shows),

a blazer that used to fit over our beer gut in college, and

the same inspiring books that are collecting dust on our coffee tables.

The holidays are just around the corner and with about 60 days of shopping left, I thought I’d compile an entrepreneur gift list. Most of the items aren’t something an entrepreneur would buy, but they need them. Whether you’re the wife/girlfriend/boyfriend/partner/friend of this rare breed of human, therefore, listen up. Items range from $14 – $650 though most fall within the $25-100 range. [If you have any product/service ideas that should be included on this list, please contact me as I’ll be releasing another list much closer to the holidays.]

Clothing

Calvin Klein Short Sleeve Cotton T-Shirts: we’ll never admit it, but most of us wear t-shirts under our button-downs (and the rest of us should). Because of this, the imagery on our t-shirts shows through and it looks terrible. These extremely affordable undershirts that are soft and light guaranteed to be a hit and something the typical entrepreneur would never buy. Helps out big time when you’re pitching VC’s and you’re as nervous as ever don’t get saddlebags!

Hugo Boss Black Lawrence Dress Shirt: classy yet snazzy. With a black shirt, you can’t go wrong. It’s trendy enough to wear it out at night but conservative enough to wear to your Series A funding dog-and-pony-show. Make sure you don’t have dandruff, but black generally makes everyone look healthier. Not a bad choice at all…

: You need a blazer so you might as well have a nice one. While not the cheapest, this blazer is versatile: you can wear it to your next meeting with your advertising clients, to your first board meeting, or to your hot date at Gramercy Tavern. While not the cheapest on this list, you pay for quality. Goes great with the black button down featured above (Hugo Boss). You’ll score big points at the upcoming nextNY event or NY Tech Meetup because you’ll be better dressed than 99% of the room.

Bacci Bucci Shoes: How scuffed are your current shoes? Look down. Are these the same shoes that you walk down Astor Place in and also, Rivington? If you then wear those to Central Park, then it’s time for new shoes. These should be your special shoes that you wear when you have your biz dev/corp. dev meetings. Why? Because when you sign that big deal, you want to look down at them and see your smile. If they aren’t shiny, then you need new ones. These shoes fit the blazer and shirt perfectly and as a bonus, they’re extra comfortable.

Office Enhancements

I never recommend giving a gift that would be strictly for the office as one could usually buy with a corporate card, but these are enhancers. If you’re jumping from startup to startup, or want to give something a bit better than one would receive as standard issue, consider the following:

Moleskin Pocket Ruled Notebook: The great authors wrote in them. Why not you? Whenever I write in mine, my IQ jumps 10 points. They survive the rough handling of your bags, the spills of frappucinos, and can contain pages of complex notes- certainly should be on your list. Comes in all sizes – I prefer the smallish ones and generally go through at least 1 per month. Beats legal pads or the schwag you get from Ad:Tech!

: Other than the really cool factor of owning a Porsche pen, I have always found that having a nice pen brings good luck. When you’re signing your Series A documents or selling your equity over to your acquirer, signing with a luxury pen makes the day that much sweeter.

Magnetic Business Card Case: Always be closing. If Boiler Room/Wall Street is right, then having your business cards on you all the time is imperative. Instead of putting them in your pocket only to have the corners creased, put them into a nice case that can be pulled out in crowds with positive appeal. The case is small yet firm and will protect enough cards that should last thru DEMO or TechCrunch 40. Not only will it hold your cards, but it’ll keep the biz cards from the associate you just met from Union Square Ventures, Sequoia and Kleiner.

: You’ve just walked into the office of DFJ Gotham and put your nappy bag down on their beautiful conference table. In walks Tim Draper and he’s looking at your dilapidated bag on his furniture good start to the meeting. Start strong. Walk in with confidence. Have a nice bag holding your goods. I like a little colour in my bags as it livens the mood, but that part is totally up to you. This bag has some extra compartments to hold your iPhone, business card case, and to protect your Aero Pen. Cool. If you’re still using your LL Bean bag from 5th grade, time to change. Trust me, it’s for the better.
Miscellaneous

: Red-eye’s on JetBlue or Virgin America aren’t exactly the most comfortable your neck is almost guaranteed to hurt the next day when you’re sitting in Accel’s boardroom or eating at Buck’s of Woodside. An extremely cheap investment of under $20 could net you a good night’s sleep and a healthy neck. You certainly want to look into this.

Starbucks Gift Card: Buying $4 latte’s isn’t in the typical startup budget, but having a venti in hand is surely comforting. If you’re bootstrapping and working out of random Starbucks, this is really helpful. Now you can afford to talk to different angel investors and buy them coffee also, there is no shortage of Starbucks in NYC.

: Everyone needs a little inspiration once in a while. Ansel Adams is a world-renowned artist and photographer and much of his work can be found in very cliché spots. The national parks are absolutely gorgeous and are extremely vast the ability to inspire anyone. If your new Adobe AIR app isn’t functioning correctly, and after 9 hours of staring intently at it isn’t giving you any insights as to why, step back and flip thru the book it’ll surely take your mind off of the code.

Startup: A Silicon Valley Adventure: The book that initially inspired me to create something great a great memoir/diary of a technology company pre-bubble in Silicon Valley. It’s amazing to read other people’s trials and tribulations and learn from them a quick read and something anyone would appreciate who is related to the technology industry. It’s an older book (90s) so you can get some copies used (and cheap). I’ve recommended this book at almost every entrepreneurial speech that I give.

: This gift is for anyone who has an appreciation of automobiles. If you’re looking to rent an exotic car for the weekend getaway or to join GDC’s next Dream Car Tour, this is an amazing gift, one that the entrepreneur wouldn’t buy himself or herself. Luxury this is, not something that benefits the company perse, but could give the entrepreneur the once in a life-time experience or the motivation to go public or sell that social network they are building to buy these cars outright.

High-End Stationery: If you’re looking to give the uber personal present, high-end stationery could be right up your alley. After every VC pitch, you should be sending thank-you notes. You should be writing to your business development partners. Get off Twitter, Facebook, and email and go long-hand. We’re entrepreneurs, go against the grain. Stationery is making a comeback. The person I’m referring to here doesn’t have a website and handles holiday cards, invitations and stationery out of her private office in Westchester, NY. Click the link to contact me for the info by appointment only.

Feel free to share this with your friends and family also, let me know your thoughts as to what should be included. The more, the merrier happy holidays, they are right around the corner.

[Note: Darren wants to make clear that he isn’t getting kickbacks or any other form of compensation for recommending this stuff. But he should be!]

Darren Herman is the co-founder of IGA Worldwide Inc., a leading in-game advertising network. Over the past 10 years, Herman has built successful companies in the digital media, technology, and marketing industries. He first got his taste of Silicon Alley while doing a brief stint at i33 Communications in the mid 90s, and he enjoys the stench of warm smokey potholes in the winter